What I Learned Running Two Startups At the Same Time

And why almost every entrepreneur has at least two jobs

Should you quit your day job to start your own company?

Should you shelve an existing startup to pursue a new startup idea?

Let’s knock the elephant out of the room right away. If you’re uncomfortable juggling two high priorities at the same time, entrepreneurship is going to be a very uncomfortable lifestyle.

Unless you find a way to make it work. I can help with that.

Why entrepreneurs end up running two companies at once

For the longest time, I thought I was an outlier. Looking back on a 20+ year career as an entrepreneur, I can count at least five times I found myself actively running two companies at the same time.

Every time it happened, I believed it to be a simple case of bad timing: Two opportunities would gel quickly in parallel. Or a succession plan blew up in my face. Or I found myself caught in a fun little opportunity that turned into a job.

Turns out I’m not such an outlier. In fact, since I’ve been advising other startups, I get this question at least once a month:

“How do I run two startups at the same time?”

And I get this question quite a lot too:

“How do I know when to quit my job and run my startup full time?”

Look, I don’t want to be the guy that preaches against loyalty, whether that loyalty is to the people you’re paying or the people who are paying you. But I will tell you this:

If startups were only founded when the timing was right and all the conditions were perfect, no one in their right mind would ever start a company. Opportunity doesn’t check to see if you’re dressed before it knocks.

Almost always the first question: How do you split work time?

Here’s the first thing you need to know.

Running two companies at the same time is almost exactly like having a full-time job plus a side gig, even when considering where to prioritize your time. There’s no “choosing”…